Methyl-5-(trimethoxy silyl propylthio) norbornane-2,3-dicarboxylic anhydride

ABSTRACT

ORGANOSILICON CARBOXYLIC ACID ANHYDRIDES ARE PREPARED BY REACTING MERCAPTOSILANES OR SILOXANES WITH UNSATURATED CARBOXYLIC ACID ANHYDRIDES IN THE PRESENCE OF FREE RADICAL GENERATORS. FOR EXAMPLE, GAMMA-MERCAPTOPROPYL TRIMETHOXYSILANE IS ADDED TO NADIC METHYL ANHYDRIDE UNDER THE INFLUENCE OF AZO-BIS-ISOBUTYRONITRILE TO GIVE

United States Patent [191 Speier et al.

[ ]*Aug. 12, 1975 METHYL-S-(TRIMETHOXY SILYL PROPYLTHIO)NORBORNANE-2,3-DICARBOXYLIC ANHYDRIDE [75] Inventors: John L. Speier;Gary E. LeGrow,

both of Midland, Mich.

[731 Assignee: Dow Corning Corporation, Midland,

Mich.

[ i" Notice: The portion of the term of this patent subsequent to June14, 1988, has been disclaimed.

[22] Filed: Dec. 10, 1973 [21] Appl. No: 423,322

Related US. Application Data [63] Continuation-impart of Ser. No.66,134, Aug. 21,

1970, abandoned.

[52] US. Cl 260/346.3; 117/135.1

[51] Int. Cl. C07D 307/89 [58] Field of Search 260/3463, 448.2 E

[56] References Cited UNITED STATES PATENTS 3,627,806 l2/l97l LeGrow260/4482 B Primary ExaminerHenry R. Jiles Assistant Examiner-Bemard I.Dentz Attorney, Agent, or Firm-Robert F. Fleming, Jr.

[5 7] ABSTRACT 1 Claim, No Drawings 1 t METHYL-S-(TRIMETHOXY SILYLPROPYLTHIO) NORBORNANE-Z,3-DICARBOXYLIC ANHYDRIDE This application is acontinuation-in-part of our application Ser. No. 66,134 filed Aug. 21,1970 and now abandoned.

The anhydride of this invention is useful as an adhesion promoter forsilicone rubber which is cured by means of alkoxysilane crosslinkers.The material of this invention is also useful as an intermediate in thepreparation of silicone-alkyd resins, which in turn, are useful asprotective coatings and paints.

This invention relates to a carboxylic anhydride of formula i(CI-I 351 ocs c-o EXAMPLE A solution of 98 g. of 3-mercaptopropyltrimethoxysilaneand 89 g. of nadic methyl anhydride containing 0.05 g. ofazo-bis-isobutyronitrile was irradiated with light of 2,537 angs. wavelength for 1 hour. The product had a refractive index of 1.4910 and thestructure was shown by nuclear magnetic resonance to be a silane of theformula

1. A COMPOUND OF THE FORMULA